WO2008003622A1 - Azolylméthyloxyranes, leur utilisation pour lutter contre des champignons phytopathogènes et agents les contenant - Google Patents

Azolylméthyloxyranes, leur utilisation pour lutter contre des champignons phytopathogènes et agents les contenant Download PDF

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WO2008003622A1
WO2008003622A1 PCT/EP2007/056403 EP2007056403W WO2008003622A1 WO 2008003622 A1 WO2008003622 A1 WO 2008003622A1 EP 2007056403 W EP2007056403 W EP 2007056403W WO 2008003622 A1 WO2008003622 A1 WO 2008003622A1
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substituent
compounds
formula
substituted
line
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PCT/EP2007/056403
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German (de)
English (en)
Inventor
Jochen Dietz
Thomas Grote
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
Alice GLÄTTLI
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Basf Se
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Priority to US12/306,322 priority Critical patent/US20090203700A1/en
Priority to DE502007002119T priority patent/DE502007002119D1/de
Priority to EP07765658A priority patent/EP2041122B1/fr
Priority to CN2007800253554A priority patent/CN101484446B/zh
Priority to JP2009517187A priority patent/JP2009541444A/ja
Priority to BRPI0713450-9A priority patent/BRPI0713450A2/pt
Priority to AT07765658T priority patent/ATE449771T1/de
Publication of WO2008003622A1 publication Critical patent/WO2008003622A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • Azolylmethyloxirane their use for controlling phytopathogenic fungi and agents containing them
  • the present invention relates to Azolylmethyloxirane of the general formula I.
  • a or B is a 6-membered heteroaryl selected from pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl, which is substituted by one to three of the following substituents: halogen, NO 2, amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, Ci-C 4 - haloalkyl, Ci-C4-haloalkoxy, Ci-C 4 alkylamino, Ci-C 4 dialkylamino, thio or Ci-C 4 alkylthio, substituted,
  • a or B is phenyl substituted by optionally one to three of the following substituents: halogen, NO 2, amino, Ci -C4 -alkyl, Ci-C 4 alkoxy, Ci-C4-haloalkyl, d-
  • Ci-C 4 dialkylamino, thio or CrC 4 4 haloalkoxy Ci-C - is alkylthio, substituted
  • the invention relates to the use of the compounds of formula I for the control of phytopathogenic fungi and agents containing them.
  • Azolylmethyloxirane their preparation and their use in crop protection are known for example from EP-A 0 094 564 and EP-A 0 196 038.
  • the present invention an object of the invention to provide new Azolylmethyloxirane with an improved fungicidal effect available. This object has been achieved with the compounds of formula I described above.
  • the compound I is able to form salts or adducts with inorganic or organic acids or with metal ions because of the basic character of the nitrogen atoms contained in them.
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.
  • Suitable organic acids are, for example, formic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms ), Arylsulfonic acids or -disulfonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids with straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or -diphosphonic acids (aromatic radicals such as phenyl and naphthyl carry one or two phosphoric acid radicals), wherein the
  • the metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, and the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, copper, Zinc and others into consideration. Particularly preferred are the metal ions of the elements of the subgroups of the fourth period.
  • the metals can be present in the various valences that belong to them.
  • An essential intermediate for the synthesis of the target compounds are ⁇ , ⁇ -disubstituted acroleins of the type.
  • R is preferably C 1 -C 4 -alkyl.
  • the reduction to acrolein may be e.g. with metal hydrides, e.g. Diisobutylalumini- umhydrid be carried out at low temperatures.
  • metal hydrides e.g. Diisobutylalumini- umhydrid be carried out at low temperatures.
  • Another possibility is to reduce the ester to the corresponding alcohol in order to obtain the desired oxidation state in a subsequent oxidation.
  • aluminum hydrides preferably lithium alanate (European Journal of Medical Chemistry, 40 (6), 529-541, 2005) or dialkylaluminum hydrides, such as, for example, DIBAL-H (Synlett, (18), 3182-3184, 2006) can be used here.
  • the corresponding oxidation reactions are known to those skilled in the art, e.g. Swern translations (Australian Journal of Chemistry, 57 (6), 537-548, 2004), with hypervalent iodine compounds (Organic Letters, 5 (17), 2989-2992, 2003), with chromium compounds, e.g.
  • the acrylic acid esters are available from glyoxylic acid esters by reaction with phosphorous compounds, e.g. Horner-Emmons type or Wittig connections.
  • Suitable phosphorus compounds can be prepared by known standard methods, for example from a compound of the following type:
  • X is a leaving group such as e.g. a halide, preferably chlorine or bromine.
  • a leaving group such as e.g. a halide, preferably chlorine or bromine.
  • the reaction of such halides to the desired Horner's Emmons or Wittig reagents may be carried out, e.g. in Chemistry of Materials, 13 (9), 3009-3017; 2001, European Journal of Organic Chemistry, (7), 1247-1257; 2005 or WO1992 / 05145.
  • alkyl halides are either commercially available or can be prepared by standard methods, e.g. by halogenation of the corresponding methyl compound.
  • Suitable halogenating agents for this reaction are N-bromosuccinimide (Chemistry-A European Journal, 12 (21), 5632-5641, 2006) or N-chlorosuccinimide (Tetrahedron Letters, 47 (37), 6607-6609, 2006).
  • Halogen fluorine, chlorine, bromine and iodine; Alkyl and the alkyl moieties of compound groups such as alkylamino: saturated, straight-chain or branched hydrocarbon radicals having preferably 1 to 4 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl and 1 , 1-dimethylethyl.
  • Haloalkyl Alkyl as mentioned above, wherein in these groups partially or completely the hydrogen atoms are replaced by halogen atoms as mentioned above.
  • the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluoro, chloro or bromo.
  • the alkyl groups are partially or completely halogenated by various halogen atoms; for mixed halogen substitutions, the combination of chlorine and fluorine is preferred.
  • (C 1 -C 4) -haloalkyl more preferably (C 1 -C 2) -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;
  • Alkoxy for an oxygen-bonded alkyl group as defined above, preferably having 1 to 4 carbon atoms.
  • alkoxy groups are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy.
  • Haloalkoxy alkoxy as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine.
  • preferred haloalkoxy radicals are OCH 2 F, OCHF 2 , OCF 3 , OCH 2 Cl, OCHCl 2 , OCCl 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2 , 2-Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 F 5 , 2-fluoropropoxy
  • Alkylthio Alkyl as defined above attached via an S atom.
  • 6-membered heteroaryl pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-tirazinyl, 1, 3,5-triazine, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3 Pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinly, 5-pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl.
  • novel compounds of formula I contain chiral centers and are generally obtained in the form of racemates or as mixtures of diastereomers of erythro and threo forms.
  • the erythro and threo diastereomers can be separated in the compounds of the invention, for example, due to their different solubility or by column chromatography and isolated in pure form. From such uniform pairs of diastereomers can be obtained by known methods uniform enantiomers.
  • antimicrobial agents can be used both the uniform diastereomers or enantiomers as well as their resulting in the synthesis of mixtures. The same applies to the fungicides.
  • the compounds according to the invention can be present in various crystal modifications which may differ in their biological activity. They are also the subject of the present invention.
  • the substituent A or B is a 6-membered heteroaryl selected from pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl, which is substituted by one to three of the following substituents: halogen, NO 2, amino, C 1 -C 4 -alkyl, C 4 -alkoxy, CrC 4 - haloalkyl, Ci-C 4 alkylamino, Ci-C 4 dialkylamino substituted, thio, or Ci-C 4 alkylthio, 4 haloalkoxy, Ci-C.
  • the substituent A or B is selected from pyridinyl or pyrimidinyl which is substituted by one to three of the above-mentioned. Substituents is substituted.
  • the substituent A or B is pyridyl which is substituted by one to three of the above-mentioned. Substituents is substituted.
  • the substituent A or B is pyrimidinyl which is substituted by one to three of the above. Substituents is substituted.
  • the substituent A or B is pyrazinyl which is substituted by one to three of the abovementioned substituents. According to a further embodiment, the substituent A or B is pyridazinyl which is substituted by one to three of the abovementioned substituents.
  • the substituent A or B is triazinyl which is substituted by one to three of the above. Substituents is substituted.
  • the 6-membered heteroaryl is substituted by one to three of the following substituents: halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, or C 1 -C 4 -haloalkoxy.
  • the 6-membered heteroaryl is substituted by one to three of the following substituents: halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.
  • the 6-membered heteroaryl is substituted by one to three of the following substituents F, Cl, methyl or methoxy.
  • the 6-membered heteroaryl is substituted by one to three of the following substituents F or Cl.
  • the other substituent A or B which differs from the 6-membered heteroaryl is unsubstituted phenyl or phenyl which is substituted by one to three of the following substituents: halogen, NO 2, amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkyl.
  • Haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylamino, Ci-C4-dialkylamino, thio or Ci-C4-alkylthio is substituted.
  • the other of the 6-membered heteroaryl substituent A or B is phenyl, which is substituted by one to three of the following substituents halogen, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4-haloalkyl or Ci -C4-haloalkoxy is substituted.
  • 6-membered heteroaryl is a different substituent A or B is phenyl, which is substituted by one to three of the following substituents halogen.
  • the other of the 6-membered heteroaryl different substituent A or B is phenyl which is substituted by one to three of the following substituents F or Cl.
  • the compounds I according to the invention which are combined in the following Tables 5 to 10 are preferred.
  • the groups mentioned in the tables for a substituent are also considered individually, regardless of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question.
  • Table 45 Compounds of the formula I in which A is the substituent 1-41 of Table 1 and B corresponds in each case to one substituent of a row of Table 2.
  • Table 84 Compounds of the formula I in which B is the substituent 3-27 of Table 3 and A in each case corresponds to a substituent of the line of Table 4.
  • Table 104 Compounds of the formula I, in which B is the substituent 3-47 of Table 3 and A in each case corresponds to a substituent of the line of Table 4.
  • the compounds I are suitable as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes, in particular from the class of the Oomycetes. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines
  • Cochliobolus species on corn, cereals, rice such as Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice, • Colletotricum species on soybeans and cotton,
  • Drechslera species Pyrenophora species on maize, cereals, rice and turf, e.g. D.teres to barley or D. tritici-repentis to wheat,
  • Gibberella species on cereals and rice e.g., Gibberella fujikuroi on rice
  • Mycosphaerella species on cereals, bananas and peanuts e.g. M. graminicola on wheat or M.fijiensis on bananas,
  • Peronospora species on cabbage and bulbous plants such as P. brassicae on cabbage or P. destructor on onion, • Phakopsara pachyrhizi and Phakopsara meibomiae on soybeans,
  • Phytophthora species on various plants e.g. P.capsici on paprika
  • Pseudoperonospora on various plants e.g. P. cubensis on cucumber or P. humili on hops,
  • Puccinia species on various plants e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus,
  • Rhizoctonia species on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beet, vegetables and various plants such as e.g. R.solani on turnips and various plants, • Rhynchosporium secalis on barley, rye and triticale,
  • Venturia species scab
  • apples and pears like. e.g. V. inaequalis to apple.
  • Peronosporomycetes such as Peronospora species, Phytophthora species, Plasmopara viticola, Pseudoperonospora species and Pythium species.
  • the compounds I are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleu- rotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients.
  • the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient in general, amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of seed are needed.
  • the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated.
  • the compounds of the formula I can be present in various crystal modifications, which may differ in their biological activity. They are also the subject of the present invention.
  • the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially: water, aromatic solvents (for example Solvesso products, xylene), paraffins
  • solvent mixtures can also be used, excipients such as ground natural minerals (for example kaolins, clays, talc,
  • Chalk and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin liquors and methyl cellulose.
  • Emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin liquors and methyl cellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg toluene, Xy- lol, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, metha- nol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg toluene, Xy- lol, paraffin, tetrahydronaphthalen
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • formulations are: 1. Products for dilution in water
  • a Water Soluble Concentrates 10 parts by weight of the active ingredients are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with 10 wt .-% active ingredient content.
  • the active compounds 20 parts by weight are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • a dispersant e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • the active ingredient content is 20% by weight
  • the active compounds 25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium Dodecylbenzenesulfonate and castor oil ethoxylate (each 5 parts by weight) dissolved.
  • This mixture is added by means of an emulsifying machine (eg Ultraturax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • the active ingredients 20 parts by weight of the active ingredients are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of the active compounds are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • the active ingredients 75 parts by weight of the active ingredients are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • I dusts (DP, DS) 5 parts by weight of the active ingredients are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content.
  • J Granules 0.5 parts by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or the fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • LS water-soluble concentrates
  • FS suspensions
  • DS dusts
  • WS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • gel formulations GF
  • the active compounds may be used as such, in the form of their formulations or the forms of use prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, litter, granules by spraying, misting, dusting, scattering or pouring.
  • the forms of application depend entirely on the purposes of use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier.
  • concentrates which are active substance, adhesion, dispersant or emulsifier and, if appropriate, solvent or oil, concentrates which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • organically modified polysiloxanes eg Break Thru S 240 ®
  • Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO-PO block polymers eg. B. Pluro- nic RPE 2035 ® and Genapol B ®
  • Alcohol ethoxylates eg. As Lutensol XP 80 ®
  • sodium dioctylsulfosuccinate e. B. Leophen RA ®.
  • the agents according to the invention in the form of application as fungicides, may also be present together with other active substances, e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • other active substances e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • fungicides for example, in many cases the spectrum of action can be broadened or resistance developments can be prevented. In many cases, synergistic effects are obtained.
  • the present invention further provides a combination of at least one azolylmethyloxirane of the formula I, in particular an azolylmethyloxirane disclosed as preferred in the present description and / or an agriculturally acceptable salt thereof and at least one further fungicidal, insecticidal, herbicidal and / or growth-regulating agent Active substance, whereby a synergistic effect can occur.
  • Another object of the present invention is a pesticidal composition
  • a pesticidal composition comprising at least one compound of the formula I, in particular a compound of the formula I described as being preferred in the present specification and / or an agriculturally acceptable acid addition or metal salt thereof and at least one solid or liquid carrier ,
  • Such a pesticidal composition may contain at least one other fungicidal, insecticidal and / or herbicidal active ingredient, whereby a synergistic effect may also occur.
  • Azoxystrobin Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Methyminostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-chloro-2-methyl-phenoxy) -5-fluoro) pyrimidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic methyl ester of methyl, 3-methoxy-2- (2- (N- (4-methoxy-phenyl) -cyclopropanecarboximidoylsulfanylmethyl) -phenyl) -acrylic acid;
  • Benzoic acid amides flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide;
  • carboxamides carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide;
  • Triazoles azaconazole, bitertanol, bromuconazoles, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothiocona - zole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1- (4-chloro-phenyl) -2 - ([1, 2,4] triazol-1-yl) -cycloheptanol;
  • - imidazoles cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, 2,3,5,6-tetrachloro-4-methanesulphonyl-pyridine , 3,4,5-trichloropyridine-2,6-di- carbonitrile, N- (1- (5-bromo-3-chloro-pyridin-2-yl) -ethyl) -2,4-dichloro-nicotinamide, N - ((5-bromo-S-chloro-pyridin-1-yl -methyl ⁇ - dichloro-nicotinamide;
  • - pyrimidines bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, panipyrim, nitrapyrin, nuarimol, pyrimethanil; - Pyrroles: fludioxonil, fenpiclonil;
  • Dicarboximides fluoroimide, iprodione, procymidone, vinclozolin;
  • acibenzolar-S-methyl acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomezine, difenzoquat,
  • Guanidines dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilat);
  • antibiotics kasugamycin, kasugamycin hydrochloride hydrate, polyoxins, streptomycin, validamycin A;
  • Organometallic compounds Fentin salts such as, for example, fentin acetate, fentin chloride, fentin hydroxide;
  • Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl;
  • Organochlorine compounds chlorothalonil, dichlofluanid, dichlorophen, flusulfamides, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phtha-Nd, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitrophenyl) -N- ethyl-4-methyl-benzenesulfonamide;
  • Inorganic active substances Phosphorous acid and its salts, sulfur, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate; - Other: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxine-copper, prohexadione-calcium, spiroxamine, tolylfluanid, N- (cyclopropylmethoxyimino- (6-difluoropnethoxy-2,3-difluorophenyl) - methyl) -2-phenylacetamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N' - 4-fluoro-3-trifluoromethyl-phenoxy) -2
  • the present invention further relates to the compositions listed in Table A, wherein in each case one row of Table A corresponds to a fungicidal composition comprising a compound of formula I (component 1), which is preferably one of the compounds described herein as preferred, and the each additional active ingredient (component 2) indicated in the respective line.
  • component 1 in each row of table A is in each case one of the compounds of the formula I which are specifically individualized in tables 1 to 11.
  • the active ingredients II mentioned above as component 2 their preparation and their action against harmful fungi are generally known (cf. they are commercially available.
  • the compounds named after IUPAC, their preparation and their fungicidal action are also known [cf. EP-A 226 917; EP-A 10 28 125; EP-A 10 35 122; EP-A 12 01 648; WO 98/46608; WO 99/24413; WO 03/14103; WO 03/053145; WO 03/066609; WO 04/049804].
  • the active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Wettol EM 31 (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent- Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
  • Wettol EM 31 wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols

Abstract

L'invention concerne des azolylméthyloxyranes de formule générale I (I) dans laquelle A ou B désigne un hétéro aryle à 6 chaînons, sélectionné parmi pyridine, pyrimidine, pyrazinyle, pyridazinyle et tria vinyle, qui est substitué par un à trois des substituants suivants; halogène, NO2, amino, alkyle C1-C4, alcoxy C1-C4, halogénure d'alkyle C1-C4, halogénure d'alcoxy C1-C4, alkylamino C1-C4, dialkylamino C1-C4, thio ou alkylthio C1-C4, et l'autre substituant respectif A ou B désigne phényle, qui est éventuellement substitué par un à trois des substituants suivants: halogène, NO2, amino, alkyle C1-C4, alcoxy C1-C4, halogénure d'alkyle C1-C4, halogénure d'alcoxy C1-C4, alkylamino C1-C4, dialkylamino C1-C4, thio ou alkylthio C1-C4. L'invention concerne également les sels d'addition d'acide ou les sels métalliques phytocompatibles de ces composés, l'utilisation des composés de formule I (I) pour lutter contre des champignons phytopathogènes, ainsi que des agents contenant lesdits azolylméthyloxyranes.
PCT/EP2007/056403 2006-07-05 2007-06-27 Azolylméthyloxyranes, leur utilisation pour lutter contre des champignons phytopathogènes et agents les contenant WO2008003622A1 (fr)

Priority Applications (7)

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US12/306,322 US20090203700A1 (en) 2006-07-05 2007-06-27 Azolylmethyloxiranes, Their Use for Controlling Phytopathogenic Fungi, and Compositions Comprising Them
DE502007002119T DE502007002119D1 (de) 2006-07-05 2007-06-27 Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel
EP07765658A EP2041122B1 (fr) 2006-07-05 2007-06-27 Azolylméthyloxyranes, leur utilisation pour lutter contre des champignons phytopathogènes et agents les contenant
CN2007800253554A CN101484446B (zh) 2006-07-05 2007-06-27 唑基甲基环氧乙烷及其在防治植物病原性真菌中的用途和包含所述化合物的试剂
JP2009517187A JP2009541444A (ja) 2006-07-05 2007-06-27 アゾリルメチルオキシラン、植物病原菌類を防除するためのその使用、およびそれを含む薬剤
BRPI0713450-9A BRPI0713450A2 (pt) 2006-07-05 2007-06-27 compostos, uso de compostos, composição de proteção de colheita, semente, e, processo para combater fungos fitopatogênicos
AT07765658T ATE449771T1 (de) 2006-07-05 2007-06-27 Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel

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WO2010086120A1 (fr) 2009-01-30 2010-08-05 Bayer Cropscience Ag Combinaisons de composés actifs
WO2010086109A1 (fr) 2009-01-30 2010-08-05 Bayer Cropscience Ag Combinaisons de composés actifs
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WO2014167008A1 (fr) 2013-04-12 2014-10-16 Bayer Cropscience Ag Nouveaux dérivés triazolinthione
WO2014167009A1 (fr) 2013-04-12 2014-10-16 Bayer Cropscience Ag Nouveaux dérivés triazole
WO2016156290A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2016156294A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Dérivés de triazole utiles en tant que fongicides
US9668481B2 (en) 2013-04-12 2017-06-06 Bayer Cropscience Aktiengesellschaft Triazole derivatives
WO2018050456A1 (fr) 2016-09-13 2018-03-22 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs comprenant un dérivé d'imidazole substitué en position 5
WO2018060074A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazolylmethyle à substitution en position 5
WO2018060075A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Dérivés de 1 -[2- (1 -chlorocyclopropyl)-2-hydroxy-3-(3-phényl -1,2-oxazol-5-yl) propyl] -1 h-imidazole-5-carbonitrile et composés apparentés en tant que fongicides pour la protection des cultures
WO2018060073A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2019092086A1 (fr) 2017-11-13 2019-05-16 Bayer Aktiengesellschaft Dérivés de tétrazolylpropyle et leur utilisation en tant que fongicides

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BRPI0713131A2 (pt) * 2006-06-23 2012-04-17 Basf Se compostos, uso de compostos, composição para a proteção de colheitas, semente, e, processo para combater fungos fitopatogênicos
ATE496912T1 (de) * 2006-07-05 2011-02-15 Basf Se Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel
BRPI0714365A2 (pt) * 2006-07-24 2013-04-02 Basf Se compostos, uso de compostos, composiÇço para a proteÇço da colheita, semente, e, processo para combater fungos fitopatogÊnicos
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US7910614B2 (en) 2006-07-25 2011-03-22 Basf Se Azolylmethyloxiranes, use thereof for controlling plant pathogenic fungi, and agents containing the same
WO2009071419A1 (fr) * 2007-12-04 2009-06-11 Basf Se Mélanges fongicides
WO2009071450A1 (fr) * 2007-12-05 2009-06-11 Basf Se Mélanges fongicides
WO2009071389A1 (fr) * 2007-12-05 2009-06-11 Basf Se Mélanges fongicides
WO2010086120A1 (fr) 2009-01-30 2010-08-05 Bayer Cropscience Ag Combinaisons de composés actifs
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WO2016156290A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2016156294A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Dérivés de triazole utiles en tant que fongicides
WO2018050456A1 (fr) 2016-09-13 2018-03-22 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs comprenant un dérivé d'imidazole substitué en position 5
WO2018060074A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazolylmethyle à substitution en position 5
WO2018060075A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Dérivés de 1 -[2- (1 -chlorocyclopropyl)-2-hydroxy-3-(3-phényl -1,2-oxazol-5-yl) propyl] -1 h-imidazole-5-carbonitrile et composés apparentés en tant que fongicides pour la protection des cultures
WO2018060073A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2019092086A1 (fr) 2017-11-13 2019-05-16 Bayer Aktiengesellschaft Dérivés de tétrazolylpropyle et leur utilisation en tant que fongicides

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US20090203700A1 (en) 2009-08-13
DE502007002119D1 (de) 2010-01-07
CL2007001951A1 (es) 2008-01-18
JP2009541444A (ja) 2009-11-26
EP2041122A1 (fr) 2009-04-01
CN101484446A (zh) 2009-07-15
CN101484446B (zh) 2011-07-13
TW200808778A (en) 2008-02-16
BRPI0713450A2 (pt) 2012-01-31
EP2041122B1 (fr) 2009-11-25
AR061819A1 (es) 2008-09-24
UY30464A1 (es) 2007-08-31
ATE449771T1 (de) 2009-12-15

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